WO2015060635A1 - Organic compound and organic electroluminescent element comprising same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent element comprising the same. The compound, according to the present invention, is used in an organic layer, preferably in a light-emitting layer, of the organic electroluminescent element, thereby improving light-emitting efficiency, driving voltage, lifespan and the like of the organic electroluminescent element.

Description

Organic compound and organic electroluminescent device comprising the same

The present invention relates to a novel organic compound that can be used as a material of the organic electroluminescent device and to an organic electroluminescent device in which the luminous efficiency, driving voltage, lifespan, etc. of the device are improved.

From the observation of organic thin-film emission by Bernanose in the 1950s, research on organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices') has been continued by blue electroluminescence using anthracene single crystals in 1965. . In 1987, Tang presented an organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer. Since then, in order to make high-efficiency, high-life organic EL devices, the development has been made in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therein.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. In this case, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.

The light emitting material may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to realize a better natural color according to the light emitting color. In addition, in order to increase luminous efficiency through an increase in color purity and energy transfer, a host / dopant system may be used as a light emitting material.

The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescent material, research on phosphorescent host materials as well as phosphorescent dopants has been conducted.

Hole injection layer, hole transport layer to date. NPB, BCP, Alq ₃ and the like are widely known as the hole blocking layer and the electron transport layer, and anthracene derivatives have been reported as fluorescent dopant / host materials as light emitting materials. In particular, phosphorescent materials having a great advantage in terms of efficiency improvement among the light emitting materials are blue, green, and red dopant materials, such as Firpic, Ir (ppy) ₃ , and (acac) Ir (btp). Metal complex compounds containing Ir, such as ₂ , are used. To date, 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.

However, existing materials have advantages in terms of luminescence properties, but due to low glass transition temperature and low thermal stability, they are not satisfactory in terms of lifespan in OLED devices. Therefore, the development of the material which is more excellent in performance is calculated | required.

An object of the present invention is to provide a novel organic compound having a high glass transition temperature, excellent thermal stability, and capable of improving the bonding force between holes and electrons.

In addition, an object of the present invention is to provide an organic electroluminescent device having improved driving voltage, luminous efficiency and the like by including the novel organic compound.

The present invention provides a compound represented by Formula 1:

Formula 1

In Chemical Formula 1,

Ar ₁ is a substituent represented by the following formula (2);

Formula 2

In Chemical Formula 2,

L is a single bond, a substituted or unsubstituted C ₆ -C ₄₀ arylene group, or a substituted or unsubstituted heteroarylene group having 5 to 40 nuclear atoms;

X ₁ to X ₅ are the same as or different from each other, each independently N or C (R ₁₁ ), and include at least one N,

In this case, when two or more of X ₁ to X ₅ is C (R ₁₁ ), a plurality of R ₁₁ are the same or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryl Oxy group, substituted or unsubstituted C ₁ -C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ -C ₄₀ arylamine group, substituted or unsubstituted C ₁ -C ₄₀ alkylsilyl group, substituted or Unsubstituted C ₁ to C ₄₀ alkylboron group, substituted or unsubstituted C ₆ to C ₄₀ arylboron group, substituted or unsubstituted C ₆ to C ₄₀ arylphosphine group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted C ₆ ~ C ₄₀ aryl selected from the group consisting of silyl groups, or groups or grain to which they are adjacent To which they are attached may form a condensed ring;

R ₁ to R ₃ are the same as or different from each other, and each independently deuterium (D), halogen, cyano, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkene Nyl group, substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ Alkyloxy group, substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl groups, substituted or unsubstituted heterocycloalkyl groups having 3 to 40 nuclear atoms, substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl groups, substituted or unsubstituted C ₁ to C ₄₀ alkylboron groups , a substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ Reel phosphine oxide group, and a substituted or non-substituted aryl group is selected from the group consisting of silyl unsubstituted C ₆ ~ C _40;

Wherein R _1, R ₂ and R ₃ when present is a plurality of, respectively, a plurality of R _1, R ₂ and R ₃ are the same or different from each other,

a, b and c are each independently an integer of 0-5,

In the above L, R ₁ to R ₃ and R ₁₁ , C ₆ ~ C ₄₀ arylene group, a heteroarylene group of 5 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkylboron group, C group _{of 6} to arylboronic of C _40, C ₆ to C ₄₀ aryl phosphine group, C ₆ to C ₄₀ aryl phosphine oxide group, and a C ₆ to an aryl silyl group of C _40, each independently selected from deuterium, halogen, a cyano group , C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₄₀ Aryl group, nuclear atom 5 to 40 heteroaryl group, C ₆ ~ for C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl of Kilgi, nuclear atoms silyl of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ aryl of C ₄₀ It may be substituted with at least one substituent selected from the group consisting of a phosphine group, a C ₆ ~ C ₄₀ aryl phosphine oxide group and a C ₆ ~ C ₄₀ arylsilyl group. In this case, when a plurality of substituents are introduced, these substituents may be the same or different from each other.

In addition, the present invention includes an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, at least one of the one or more organic material layers is an organic electric field characterized in that it comprises a compound of the formula (1) Provided is a light emitting device.

Here, at least one of the one or more organic material layers including the compound of Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer and a light emitting layer, it is preferable that the light emitting layer. In this case, the compound represented by Formula 1 may be a green or red phosphorescent host material.

Since the compound represented by Formula 1 according to the present invention has excellent thermal stability and phosphorescence properties, it may be used as a material of the organic material layer of the organic EL device. In particular, when the compound represented by Chemical Formula 1 according to the present invention is used as a phosphorescent host material, an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency, and long life compared to a conventional host material can be manufactured. Full color display panels with significantly improved performance and lifetime can also be manufactured.

Hereinafter, the present invention will be described in detail.

<New compound>

The novel compound according to the present invention forms a basic skeleton with a carbozole moiety in which phenyl is bonded at positions 1 and 3, and various substituents are bonded to the basic skeleton, represented by Chemical Formula 1 It is characterized by.

When it is used alone because of poor luminous properties of 1,3,5-triphenyl-benzene, it is not suitable as an organic electroluminescent device material, but a carbazole moiety is used as an organic electroluminescent device material, especially as a phosphorescent host material. It is used in various ways. The carbazole moiety has a high triplet energy of 3.0 eV and a low HOMO energy level of 6.0 eV, which is mainly used in blue phosphorescent hosts. Therefore, in the 1,3-diphenyl-9H-carbazole structure represented by Formula 1 of the present invention in which one biphenyl of 1,3,5-triphenyl-benzene is modified with carbazole, triplet energy is less than 3.0 eV, and HOMO energy The level rises so that the energy band gap is suitable for green / red phosphorescent hosts.

In particular, the present invention is characterized in that the electron withdrawing group (EWG) represented by the formula (2) is substituted in position 9 of the 1,3-diphenyl-9H-carbazole structure. The structure having both electron withdrawing group (EWG) and electron donating group (EDG) with high electron donor has a bipolar characteristic, so that the whole molecule has a bipolar characteristic. Since it can be increased, not only is it advantageous as a host in the phosphorescent light emitting layer, but also can be applied as a hole transporting layer, a hole injection layer and the like.

In addition, in the present invention, a phenyl group substituted at the position 1 of the carbazole moiety and an electron withdrawing group (EWG) substituted at the position 9 at the carbazole moiety are adjacent to each other to cause steric hinderance. Therefore, the compound molecules are distorted to solve the problem of deterioration of the luminescence property due to π-π-stacking, thereby preventing the formation of excitation dimers (eximers), thereby improving the luminescence efficiency. do.

In addition, in the phosphorescent layer, the host material requires that the triplet energy gap of the host is higher than that of the dopant because the lowest excited state of the host must be higher than the lowest emission state of the dopant in order to provide effective phosphorescence from the dopant. The novel compound according to the present invention is lower than the triplet energy of the compound having a simple carbazole moiety as a basic skeleton by phenyl substitution at positions 1 and 3 of the carbazole moiety, and is suitable for green phosphorescence emission. It can have

On the other hand, the compound represented by Formula 1 of the present invention is a molecular weight of the compound is significantly increased due to the aromatic ring (aromatic ring) or heteroaromatic ring (substituents) substituents introduced in the molecule, so that the glass transition temperature is conventionally improved It shows higher thermal stability than CBP (4,4-dicarbazolybiphenyl). In addition, the compound represented by the formula (1) of the present invention is also effective in suppressing the crystallization of the organic material layer.

In general, a ceramic crucible having high thermal conductivity is used as a method of forming an organic layer of an organic light emitting device by vacuum deposition, and should be designed so that stepwise continuous evaporation control is possible and no organic splashing occurs. As the temperature of the evaporation source is not properly raised, the organic material that reaches the evaporation temperature in an excessively short time is splashed, and the inlet of the evaporation source is blocked, and thus the deposition rate of the organic material is not constant and thus the desired thin film characteristics are not obtained. . It also increases the likelihood that organic matter will discolor or decolorize during deposition. The organic material has the property of being deposited by melting or sublimation depending on the material. In the case of the sublimation method, the compound immediately forms a organic layer through a sublimation process in the solid state, whereas in the melting method, the solid passes through a liquid. Vaporize to form an organic layer. Melting method is difficult to control the deposition temperature or uniformity because the material undergoes a phase change one step more than the sublimation method. At this time, in the case of the compound of the present invention 1,3-diphenyl-9H-carbazole structure is deposited by the sublimation method, in the case of the Ref-1 structure containing an unsubstituted carbazole moiety is confirmed to be deposited by the melting method (Table 1), the compound of the present invention can have uniform thin film properties, thereby improving the luminescence properties.

Table 1

As a result, when the compound of Formula 1 according to the present invention is used as a hole injection / transport layer material of an organic electroluminescent device or a phosphorescent host material of blue, green and / or red color, it is compared with conventional organic material layers (for example, CBP). The efficiency and lifespan of the organic electroluminescent device can be greatly improved. In addition, the lifespan of the organic EL device may maximize the performance of the full color OLED panel.

The novel compound according to the present invention has a structure in which a substituent represented by formula (2) is bonded to a carbazole moiety basic skeleton of formula (1) in which phenyl is bonded to positions 1 and 3, respectively.

In the compound represented by Chemical Formula 1, Ar ₁ introduced at the N site of the carbazole basic skeleton may be embodied as in Chemical Formula 2.

In Formula 2, L is a linker of a divalent group known in the art, a single bond, a substituted or unsubstituted C ₆ ~ C ₄₀ arylene group, and a substituted or unsubstituted nuclear atom It may be selected from the group consisting of 5 to 40 heteroarylene groups.

Here, examples of the C ₆ to C ₄₀ arylene group and the heteroarylene group having 5 to 40 nuclear atoms include a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, and a pyrantrenylene group , Carbazolylene group, thiophenylene group, indolylene group, furinylene group, quinolinyl group, pyrroylene group, imidazolylene group, oxazolylene group, thiazolylene group, triazolylene group, pyridinylene group, pyrimididi Nylene groups and the like. In the present invention, L is preferably selected from a single bond, a phenylene group, or a biphenylene group.

In the L, C ₆ ~ C ₄₀ arylene group, a heteroarylene group of 5 to 40 nuclear atoms are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group , C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C ₆ ~ C _40, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ with an aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group substituents of two or more selected from the group consisting of And when there are a plurality of the substituents, they may be the same or different from each other.

X ₁ to X ₅ are the same as or different from each other, and each independently N or C (R ₁₁ ), and include at least one N.

In this case, when two or more of X ₁ to X ₅ are C (R ₁₁ ), a plurality of R ₁₁ may be the same or different from each other even though they are the same, and each independently hydrogen, deuterium (D), halogen, cyano group, substitution or Unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ to C ₄₀ arylamine group, substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group , Substituted or unsubstituted C ₁ ~ C ₄₀ alkyl boron group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group and substituted or unsubstituted C ₆ ~ C ₄₀ arylsilyl group, or these It may be combined with adjacent groups to form a condensed ring.

In R ₁₁ , an alkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an arylphosphine group, an arylphosphine oxide group and an arylsilyl The groups are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atom 5 To 40 heteroaryl group, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom number 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl of the group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C may be substituted by one or more substituents selected from the group consisting of arylsilyl _40, wherein when the substituent is plural, they are equal to each other Or it may be different.

According to a preferred embodiment of the present invention, the substituent represented by Formula 2 may be a substituent represented by any one of the following formulas A-1 to A-15.

In Chemical Formulas A-1 to A-15,

L and R ₁₁ are as defined in Formula 1 above,

When there are a plurality of R ₁₁ , they are the same as or different from each other,

R ₂₁ is hydrogen, deuterium (D), halogen, cyano group, substituted or unsubstituted C ₁ -C ₄₀ alkyl group, substituted or unsubstituted C ₆ -C ₄₀ aryl group, substituted or unsubstituted nuclear atom 5 to 40 heteroaryl groups, substituted or unsubstituted C ₆ to C ₄₀ aryloxy groups, substituted or unsubstituted C ₁ to C ₄₀ alkyloxy groups, substituted or unsubstituted C ₆ to C ₄₀ aryl An amine group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ to C ₄₀ aryl boron group, substituted or aryl phosphonium the unsubstituted C ₆ ~ C ₄₀ pingi, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted selected from the group consisting arylsilyl of a C ₆ ~ C ₄₀ ring, or Or they may combine with adjacent groups to form a condensed ring,

n is an integer of 0-4.

In R ₂₁ , an alkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an arylphosphine group, an arylphosphine oxide group and an arylsilyl The groups are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atom 5 To 40 heteroaryl group, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom number 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl of the group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C may be substituted by one or more substituents selected from the group consisting of arylsilyl _40, wherein when the substituent is plural, they are equal to each other Or it may be different.

More specifically, the substituents represented by Formulas A-1 to A-15 are preferably selected from the group of substituents represented by the following structures. However, this is not particularly limited.

Meanwhile, in the compound represented by Formula 1 according to the present invention, R ₁ to R ₃ are the same or different, and each independently deuterium (D), halogen, cyano, alkyl group of C ₁ ~ C ₄₀ , C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atom 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyl Oxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, is selected from the group consisting of C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ with an aryl silyl group of C ₄₀ of. Wherein R _1, R ₂ and R ₃ when present is a plurality of, respectively, a plurality of R _1, R ₂ and R ₃ may be the same or different from each other.

In R ₁ to R ₃ , an alkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an arylphosphine group, or an arylphosphine oxide group And arylsilyl groups are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nucleus Heteroaryl group of 5 to 40 atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, nucleus A heterocycloalkyl group having 3 to 40 atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkyl boron group, a C ₆ to C ₄₀ aryl boron group, a C ₆ to C ₄₀ arylphosphine group, C ₆ ~ C ₄₀ aryl phosphine which may be substituted with oxide groups and one or more substituents selected from the group consisting of C ₆ ~ C ₄₀ aryl group in the silyl. In this case, when there are a plurality of substituents, they may be the same or different from each other.

In the present invention, each of R ₁ to R ₃ is preferably a C ₆ to C ₄₀ aryl group, more preferably a phenyl group.

a, b, and c are each independently an integer of 0-5.

According to the present invention, the compound represented by Chemical Formula 1 may be further embodied as a compound represented by any one of the following Chemical Formulas 3 to 7.

[Formula 3]

(a = b = c = 0)

[Formula 4]

(a = b = 0, c = 1)

[Formula 5]

(a = b = 0, c = 2)

[Formula 6]

(a = b = 0, c = 1)

[Formula 7]

(a = b = 0, c = 1)

In Chemical Formulas 3 to 7,

Ar ₁ is the same as defined in Formula 2, and each Ar ₁ is the same or different,

Z ₁ is selected from O, S, Se, N (R ₄ ), C (R ₅ ) (R ₆ ) and Si (R ₇ ) (R ₈ )

R ₄ to R ₈ are the same as or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group , Substituted or unsubstituted C ₆ -C ₄₀ arylamine group, substituted or unsubstituted C ₁ -C ₄₀ alkylsilyl group, substituted or unsubstituted C ₁ -C ₄₀ alkylboron group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group and substituted or unsubstituted C ₆ Or an arylsilyl group of ˜C ₄₀ , or they may combine with adjacent groups to form a condensed ring. Wherein R ₄ to R ₈ are the same as or different from each other, and each independently a C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted nuclear atom 5 to 5 It is preferably selected from 40 heteroaryl groups.

In R ₄ to R ₈ , an alkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an arylphosphine group, or an arylphosphine oxide group And arylsilyl groups are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nucleus Heteroaryl group of 5 to 40 atoms, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, nucleus A heterocycloalkyl group having 3 to 40 atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkyl boron group, a C ₆ to C ₄₀ aryl boron group, a C ₆ to C ₄₀ arylphosphine group, C ₆ ~ C ₄₀ aryl phosphine which may be substituted with oxide groups and one or more substituents selected from the group consisting of C ₆ ~ C ₄₀ aryl group in the silyl. In this case, when there are a plurality of substituents, they may be the same or different from each other.

The compound represented by Chemical Formula 1 of the present invention described above may be further embodied in a compound structure consisting of C-1 to C-168 illustrated below. However, the compound represented by the formula (1) of the present invention is not limited by those illustrated below.

"Alkyl" in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl And the like, but are not limited thereto.

"Alkenyl" in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon double bonds, and examples thereof include vinyl, Allyl, isopropenyl, 2-butenyl, and the like, but is not limited thereto.

"Alkynyl" in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon triple bonds, and examples thereof include ethynyl. , 2-propynyl, and the like, but is not limited thereto.

"Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, singly or in combination of two or more rings. In addition, a form in which two or more rings are pendant or condensed with each other may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply attached or condensed with each other may be included, and is also construed to include a form condensed with an aryl group. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl, and is linear, branched or cyclic structure. Interpret as including. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

"Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

"Cycloalkyl" in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

"Heterocycloalkyl" in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 40 carbon atoms.

"Condensed ring" in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.

The compound of formula 1 of the present invention can be synthesized in various ways with reference to the following synthesis examples. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.

<Organic EL device>

On the other hand, another aspect of the present invention relates to an organic electroluminescent device comprising a compound represented by the formula (1) according to the present invention.

Specifically, the organic electroluminescent device according to the present invention comprises an anode, a cathode and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer It includes a compound represented by the formula (1). In this case, the compound may be used alone, or two or more may be used in combination.

The at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer may include a compound represented by the formula (1). Preferably, the organic material layer including the compound of Formula 1 may be a light emitting layer.

According to one embodiment of the present invention, the light emitting layer of the organic electroluminescent device may include a host material, wherein the host material may include the compound of formula (1). As such, when the compound of Formula 1 is included as the light emitting layer material of the organic EL device, preferably blue, green, or red phosphorescent host material, the binding force between the holes and the electrons in the light emitting layer is increased. Efficiency (luminescence efficiency and power efficiency), lifetime, brightness, driving voltage, and the like can be improved. The compound represented by Chemical Formula 1 may be included in the organic light emitting device as a green and / or red phosphorescent host, a fluorescent host, or a dopant material.

The structure of the organic EL device according to the present invention is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. In this case, at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably the light emitting layer comprises a compound represented by the formula (1) Can be. Specifically, the compound of Formula 1 may be used as a phosphorescent host material of the light emitting layer. An electron injection layer may be further stacked on the electron transport layer.

In addition, the structure of the organic electroluminescent device according to the present invention may be a structure in which an anode, one or more organic material layers and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.

The organic electroluminescent device according to the present invention is formed by using materials and methods known in the art, except that at least one layer (eg, the light emitting layer) of the organic material layer is formed to include the compound represented by Chemical Formula 1. It may be prepared by forming another organic layer and an electrode.

The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

The substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.

In addition, non-limiting furnaces of the positive electrode material usable include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.

In addition, non-limiting examples of the negative electrode material that can be used include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; And multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like.

In addition, the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, conventional materials known in the art may be used.

Hereinafter, the present invention will be described in detail with reference to the following Examples. However, the following examples are merely to illustrate the invention, the present invention is not limited by the following examples.

Preparation Example 1 Synthesis of PCZ-1

<Step 1> Synthesis of 1,3-diphenyl-5- (2-nitrophenyl) benzene

250 ml / 120 ml with 13.7 g (50.0 mmol) of 1,3-diphenylbenzene-5-boronic acid, 15.2 g (75.0 mmol) of 1-bromo-2-nitrobenzene, 6.0 g (150.0 mmol) of NaOH under nitrogen stream THF / H ₂ O was added and stirred. 2.89 g (5 mol%) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to obtain the title compound 1,3-diphenyl-5- (2-nitrophenyl) benzene (13.5 g, 38.5 mmol, yield 77%).

Mass: [M] ⁺ = 351 g / mol

Elemental Analysis: C, 82.03; H, 4.88; N, 3.99; O, 9.11

<Step 2> Synthesis of PCZ-1

Under nitrogen stream, 10.5 g (30.0 mmol) of 1,3-diphenyl-5- (2-nitrophenyl) benzene, 23.6 g (90.0 mmol) of triphenylphosphine, and 200 ml of 1,2-dichlorobenzene were added thereto, followed by stirring for 12 hours. After the reaction was completed, 1,2-dichlorobenzene was removed and extracted with dichloromethane. The extracted organic layer was removed with MgSO ₄ and water, and column chromatography was used to obtain PCZ-1 (6.61 g, 20.7 mmol, yield 69%) as a target compound.

Mass: [M] ⁺ = 319 g / mol

Elemental Analysis: C, 90.25; H, 5. 36; N, 4.39

¹ H-NMR: δ 7.23 (m, 3H), 7.42 (m, 2H), 7.52 (m, 8H), 7.62 (d, 1H), 7.74 (d, 1H), 8.15 (d, 1H), 11.07 ( s, 1 H)

Preparation Example 2 Synthesis of PCZ-2

<Step 1> Synthesis of PCZ-2

4.83 g (10.0 mmol) of 1,3,6,8-tetrabromo-9H-carbazole, 7.32 g (60.0 mmol) of phenylboronic acid, 4.8 g (120.0 mmol) of NaOH and 250 ml / 120 ml of THF under nitrogen stream / H ₂ O was added and stirred. 2.32 g (5 mol%) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound PCZ-2 (3.06 g, 6.49 mmol, 65% yield).

Mass: [M] ⁺ = 471 g / mol

Elemental Analysis: C, 91.69; H, 5. 34; N, 2.97

¹ H-NMR: δ 7.22 (d, 4H), 7.45 (m, 4H), 7.57 (m, 14H), 7.78 (d, 2H), 11.09 (s, 1H)

Preparation Example 3 Synthesis of PCZ-3

<Step 1> Synthesis of 1,3-diphenyl-5- (3-chloro-6-nitrophenyl) benzene

Except for using 2-bromo-4-chloro-1-nitrobenzene (17.7 g, 75.0 mmol) instead of 1-bromo-2-nitrobenzene, the same procedure as in <Step 1> of Preparation Example 1 , 3-diphenyl-5- (3-chloro-6-nitrophenyl) benzene (13.3 g, 34.5 mmol, yield 69%) was obtained.

Mass: [M] ⁺ = 385 g / mol

Elemental Analysis: C, 74.71; H, 4. 18; Cl, 9.19; N, 3.63; O, 8.29

<Step 2> Synthesis of 6-chloro-1,3-diphenyl-9H-carbazole

The above preparation, except using 1,3-diphenyl-5- (3-chloro-6-nitrophenyl) benzene (11.6 g, 30.0 mmol) instead of 1,3-diphenyl-5- (2-nitrophenyl) benzene 6-chloro-1,3-diphenyl-9H-carbazole (6.26 g, 17.7 mmol, 59% yield) was obtained in the same manner as in <Step 2> of Example 1.

Mass: [M] ⁺ = 353 g / mol

Elemental Analysis: C, 81.46; H, 4.56; Cl, 10.02; N, 3.96

<Step 3> Synthesis of PCZ-3

<Step 1 of Preparation Example 2, except that 6-chloro-1,3-diphenyl-9H-carbazole (10.6 g, 30.0 mmol) was used instead of 1,3,6,8-tetrabromo-9H-carbazole. PCZ-3 (7.49 g, 18.93 mmol, Yield 63%) was obtained by the same procedure as>.

Mass: [M] ⁺ = 395 g / mol

Elemental Analysis: C, 91.11; H, 5. 35; N, 3.54

¹ H-NMR: δ 7.23 (d, 2H), 7.41 (m, 3H), 7.53 (m, 11H), 7.72 (m, 3H), 7.86 (d, 1H), 11.09 (s, 1H)

Preparation Example 4 Synthesis of BCZ-1

<Step 1> Synthesis of 1,3-diphenyl-5- (3-bromo-6-nitrophenyl) benzene

250 ml / 120 with 13.7 g (50.0 mmol) of 1,3-diphenylbenzene-5-boronic acid, 15.2 g (75.0 mmol) of 2,4-dibromo-1-nitrobenzene 21.1 g (75.0 mmol) under nitrogen stream ml of THF / H ₂ O was added and stirred. 2.89 g (5 mol%) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to obtain the target compound 1,3-diphenyl-5- (3-bromo-6-nitrophenyl) benzene (16.6 g, yield 77%).

MS [M + 1] ⁺ 430, 432

Elemental Analysis: C, 66.99; H, 3.75; Br, 18.57; N, 3.26; O, 7.44

<Step 2> Synthesis of 6-bromo-1,3-diphenyl-9H-carbazole

Under nitrogen stream, 12.9 g (30.0 mmol) of 1,3-diphenyl-5- (3-bromo-6-nitrophenyl) benzene, 23.6 g (90.0 mmol) of triphenylphosphine, and 200 ml of 1,2-dichlorobenzene were added thereto, followed by stirring for 12 hours. . After the reaction was completed, 1,2-dichlorobenzene was removed and extracted with dichloromethane. The extracted organic layer was removed with water by MgSO ₄ , and 6-bromo-1,3-diphenyl-9H-carbazole (8.00 g, yield 67%) was obtained using column chromatography.

MS [M + 1] ⁺ 398, 396

Elemental Analysis: C, 72.37; H, 4.05; Br, 20.06; N, 3.52

<Step 3> Synthesis of 6-bromo-1,3,9-triphenyl-9H-carbazole

6-bromo-1,3-diphenyl-9H-carbazole (18.4 g, 46.2 mmol), iodobenzene (14.1 g, 69.3 mmol), Cu powder (0.29 g, 4.62 mmol), K ₂ CO ₃ (6.38 g) under nitrogen stream , 46.2 mmol), Na ₂ SO ₄ (6.56 g, 46.2 mmol) and nitrobenzene (200 ml) were mixed and stirred at 190 ° C. for 12 hours. After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent in the organic layer was removed from water and purified by column chromatography to give 6-bromo-1,3,9-triphenyl-9H-carbazole (15.6 g, 71% yield).

MS [M + 1] ⁺ 476, 474

Elemental Analysis: C, 75.95; H, 4. 25; Br, 16.84; N, 2.95

Step 4 Synthesis of 1,3,9-triphenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole

6.08 g (12.8 mmol) of 6-bromo-1,3,9-triphenyl-9H-carbazole and 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2 under nitrogen stream '-bi (1,3,2-dioxaborolane) 4.86 g (19.1 mmol), Pd (dppf) Cl ₂ 0.52 g (5 mol%), KOAc 3.76 g (38.3 mmol), 100 ml of DMF was added and 12 h at 130 ° C. stirring after completion of the reaction, water was removed by MgSO ₄ and extracted with ethyl acetate. The reaction product from which the solvent was removed was subjected to column chromatography using 1,3,9-triphenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H- as a target compound. carbazole (4.74 g, yield 71%) was obtained.

MS [M + 1] ⁺ 522

Elemental Analysis: C, 82.92; H, 6. 19; B, 2.07; N, 2.69; O, 6.14

Step 5 Synthesis of BCZ-1

3.89 g (10.0 mmol) of 6-bromo-1,3-diphenyl-9H-carbazole, 7.82 g (15.0 mmol) of 1,3,9-triphenyl-6- (4,4,5,5- under nitrogen stream tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole, 4.2 g (15.0 mmol) of NaOH and 250 ml / 120 ml of THF / H ₂ O were added and stirred. 0.6 g (5 mol%) of Pd (PPh ₃ ) ₄ was added at 40 ° C. and stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to obtain the title compound 1,3-diphenyl-5- (3-bromo-6-nitrophenyl) benzene (6.34 g, 87% yield).

MS [M + 1] ⁺ 713

Elemental Analysis: C, 90.98; H, 5.09; N, 3.93

¹ H-NMR: δ 7.20 (m, 4H), 7.42 (m, 5H), 7.52 (m, 18H), 7.75 (m, 5H), 7.88 (d, 1H), 8.00 (d, 1H), 8.19 ( d, 1H), 10.12 (s, 1H)

Preparation Example 5 Synthesis of BCZ-2

<Step 1> Synthesis of BCZ-2

1,3,9-triphenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9-phenyl-9H-carbazol-3-ylboronic acid instead of 9H-carbazole BCZ-2 (4.71 g, Yield 84%) was obtained in the same manner as the <Step 5> of Preparation Example 1, except that (4.30 g, 15.0 mmol) was used.

MS [M + 1] ⁺ 561

Elemental Analysis: C, 89.97; H, 5.03; N, 5.00

¹ H-NMR: δ 7.22 (m, 4H), 7.42 (m, 3H), 7.55 (m, 11H), 7.71 (m, 5H), 7.85 (m, 2H), 8.01 (d, 1H), 8.52 ( d, 1H), 10.13 (s, 1H)

Preparation Example 6 Synthesis of BCZ-3

Step 1 Synthesis of BCZ-3

1,3,9-triphenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole instead of 9,9-dimethyl-9H-fluoren-2- Except for using ylboronic acid (3.57 g, 15.0 mmol) was carried out the same procedure as in <Step 5> of Preparation Example 1 to obtain BCZ-3 (4.15 g, 81% yield).

MS [M + 1] ⁺ 512

Elemental Analysis: C, 91.55; H, 5.71; N, 2.74

¹ H-NMR: δ 1.72 (s, 6H), 7.23 (m, 3H), 7.38 (t, 1H), 7.45 (m, 2H), 7.54 (m, 8H), 7.68 (m, 2H), 7.71 ( m, 3H), 7.84 (m, 2H), 7.93 (d, 1H), 10.13 (s, 1H)

Preparation Example 7 Synthesis of BCZ-4

Step 1 Synthesis of BCZ-4

Dibenzo [b, d] furan-2-ylboronic acid instead of 1,3,9-triphenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole Except for using (3.18 g, 15.0 mmol) BCZ-4 (4.13 g, yield 85%) was obtained in the same manner as the <Step 5> of Preparation Example 1.

MS [M + 1] ⁺ 486

Elemental Analysis: C, 89.05; H, 4.77; N, 2.88; O, 3.29

¹ H-NMR: δ 7.20 (m, 2H), 7.32 (m, 2H), 7.41 (m, 2H), 7.53 (m, 7H), 7.68 (m, 2H), 7.72 (m, 4H), 7.85 ( m, 3H), 10.13 (s, 1H)

Preparation Example 8 Synthesis of BCZ-5

Step 1 Synthesis of BCZ-5

Dibenzo [b, d] thiophen-4-ylboronic acid instead of 1,3,9-triphenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole Except for using (3.45 g, 15.0 mmol) BCZ-5 (4.36 g, 87% yield) was obtained by the same procedure as in <Step 5> of Preparation Example 1.

MS [M + 1] ⁺ 502

Elemental Analysis: C, 86.19; H, 4. 62; N, 2.79; S, 6.39

¹ H-NMR: δ 7.21 (m, 2H), 7.41 (m, 2H), 7.53 (m, 10H), 7.72 (m, 3H), 7.87 (d, 1H), 7.93 (d, 1H), 8.20 ( d, 1H), 8.43 (m, 2H), 10.11 (s, 1H)

Synthesis Example 1 Synthesis of C-10

PCZ-1 (3.19 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10.00 mmol), NaH (0.24 g, 10.00 mmol) and DMF under nitrogen stream 50 ml) were mixed and stirred at room temperature for 1 hour. After the reaction was completed, water was added and the solid compound was filtered and purified by column chromatography to obtain the title compound C-10 (5.01 g, yield 91%).

Mass: [M] ⁺ = 550 g / mol

Synthesis Example 2 Synthesis of C-12

PCZ-1 (3.19 g, 10.00 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol), Pd ₂ (dba) ₃ (under nitrogen stream 0.46 g, 0.5 mmol), (t-Bu) ₃ P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 50 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound C-12 (4.95 g, yield 79%).

Mass: [M] ⁺ = 626 g / mol

Synthesis Example 3 Synthesis of C-16

2- (3'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (5.04 instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine g, 12.00 mmol), was used in the same manner as in Synthesis Example 2 to obtain C-16 (4.70 g, yield 67%) as a target compound.

Mass: [M] ⁺ = 702 g / mol

Synthesis Example 4 Synthesis of C-28

2- (3-chlorophenyl) -4,6-di (naphthalen-2-yl) -1,3,5-triazine instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Except for using (5.04 g, 12.00 mmol), to obtain the target compound C-28 (5.66 g, yield 78%) by the same procedure as in Synthesis Example 2.

Mass: [M] ⁺ = 726 g / mol

Synthesis Example 5 Synthesis of C-66

Except for using PCZ-2 (4.71 g, 10.00 mmol) instead of PCZ-1, the same procedure as in Synthesis Example 1 was carried out to obtain the target compound C-66 (5.83 g, yield 83%).

Mass: [M] ⁺ = 702 g / mol

Synthesis Example 6 Synthesis of C-68

Except for using PCZ-2 (4.71 g, 10.00 mmol) instead of PCZ-1, the same procedure as in Synthesis Example 2 was carried out to obtain the target compound C-68 (5.60 g, yield 72%).

Mass: [M] ⁺ = 778 g / mol

Synthesis Example 7 Synthesis of C-94

Except for using PCZ-3 (3.95 g, 10.00 mmol) instead of PCZ-1, the same procedure as in Synthesis Example 1 was carried out to obtain the title compound C-94 (5.38 g, yield 86%).

Mass: [M] ⁺ = 626 g / mol

Synthesis Example 8 Synthesis of C-96

Except for using PCZ-3 (3.95 g, 10.00 mmol) instead of PCZ-1, the same procedure as in Synthesis Example 2 was carried out to obtain the target compound C-96 (4.56 g, yield 65%).

Mass: [M] ⁺ = 702 g / mol

Synthesis Example 9 Synthesis of C-99

2- (3'-chlorobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (5.04 instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine g, 12.00 mmol) was performed in the same manner as in Synthesis Example 8 to obtain C-99 (5.52 g, 71% yield) of the title compound.

Mass: [M] ⁺ = 778 g / mol

Synthesis Example 10 Synthesis of C-25

The synthesis, except that 2- (3-chlorophenyl) -4-phenylquinazoline (3.79 g, 12.00 mmol) instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine The same procedure as in Example 2 was carried out to obtain C-25 (3.65 g, 61% yield) as the target compound.

Mass: [M] ⁺ = 599 g / mol

Synthesis Example 11 Synthesis of C-26

Except for using 4- (biphenyl-4-yl) -2-chloroquinazoline (3.79 g, 12.00 mmol) instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine, C-26 (3.29 g, Yield 55%) was obtained by the same procedure as in Synthesis Example 2.

Mass: [M] ⁺ = 599 g / mol

Synthesis Example 12 Synthesis of C-27

Use 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (4.39 g, 12.00 mmol) instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine Except for, the same procedure as in Synthesis Example 2 was carried out to obtain C-27 (3.69 g, yield 51%) as the target compound.

Mass: [M] ⁺ = 725 g / mol

Synthesis Example 13 Synthesis of C-117

BCZ-1 (7.13 g, 10.00 mmol), 2-chloro-4,6-diphenylpyridine (3.19 g, 12.00 mmol), Pd ₂ (dba) ₃ (0.46 g, 0.5 mmol), (t-Bu) under nitrogen stream ₃ P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound C-117 (7.07 g, yield 75%) by column chromatography.

MS [M + 1] ⁺ 942

Synthesis Example 14 Synthesis of C-120

The same procedure as in Synthesis Example 13 was performed except that 2-chloro-4,6-diphenyl-1,3,5-triazine (3.21 g, 12.00 mmol) was used instead of 2-chloro-4,6-diphenylpyridine. C-120 (7.65 g, yield 81%) was obtained as the target compound.

MS [M + 1] ⁺ 944

Synthesis Example 15 Synthesis of C-122

Except for using 2- (3-chlorophenyl) -4,6-diphenylpyrimidine (4.11 g, 12.00 mmol) instead of 2-chloro-4,6-diphenylpyridine, the same procedure as in Synthesis Example 13 was carried out to obtain C. -122 (6.27 g, yield 81%) was obtained.

MS [M + 1] ⁺ 1019

Synthesis Example 16 Synthesis of C-123

Except for using 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.11 g, 12.00 mmol) instead of 2-chloro-4,6-diphenylpyridine C. -123 (6.22 g, yield 80%) was obtained.

MS [M + 1] ⁺ 1019

Synthesis Example 17 Synthesis of C-124

Same as Synthesis Example 13 except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol) was used instead of 2-chloro-4,6-diphenylpyridine. The procedure was followed to obtain the target compound C-124 (6.24 g, yield 80%).

MS [M + 1] ⁺ 1020

Synthesis Example 18 Synthesis of C-129

Except for using BCZ-2 (5.61 g, 10.00 mmol) instead of BCZ-1 was the same procedure as in Synthesis Example 13 to obtain the target compound C-129 (5.53 g, yield 70%).

MS [M + 1] ⁺ 790

Synthesis Example 19 Synthesis of C-132

Except for using BCZ-2 (5.61 g, 10.00 mmol) instead of BCZ-1 to obtain the target compound C-132 (5.86 g, yield 74%) was carried out in the same manner as in Synthesis Example 14.

MS [M + 1] ⁺ 792

Synthesis Example 20 Synthesis of C-134

Except for using BCZ-2 (5.61 g, 10.00 mmol) instead of BCZ-1 to obtain the target compound C-134 (6.85 g, yield 79%) was carried out in the same manner as in Synthesis Example 15.

MS [M + 1] ⁺ 867

Synthesis Example 21 Synthesis of C-135

Except for using BCZ-2 (5.61 g, 10.00 mmol) instead of BCZ-1 was the same procedure as in Synthesis Example 16 to obtain the target compound C-135 (6.80 g, yield 78%).

MS [M + 1] ⁺ 867

Synthesis Example 22 Synthesis of C-136

Except for using BCZ-2 (5.61 g, 10.00 mmol) instead of BCZ-1 was carried out in the same manner as in Synthesis Example 17 to obtain the target compound C-136 (7.20 g, 83% yield).

MS [M + 1] ⁺ 868

Synthesis Example 23 Synthesis of C-144

Except for using BCZ-3 (5.12 g, 10.00 mmol) instead of BCZ-1 was the same procedure as in Synthesis Example 14 to obtain the target compound C-144 (6.46 g, 87% yield).

MS [M + 1] ⁺ 743

Synthesis Example 24 Synthesis of C-148

Except for using BCZ-3 (5.12 g, 10.00 mmol) instead of BCZ-1 was the same procedure as in Synthesis Example 17 to obtain the target compound C-148 (6.46 g, yield 81).

MS [M + 1] ⁺ 819

Synthesis Example 25 Synthesis of C-156

Except for using BCZ-4 (4.86 g, 10.00 mmol) instead of BCZ-1 was the same procedure as in Synthesis Example 14 to obtain the target compound C-156 (6.24 g, 87% yield).

MS [M + 1] ⁺ 717

Synthesis Example 26 Synthesis of C-160

Except for using BCZ-4 (4.86 g, 10.00 mmol) instead of BCZ-1 was the same procedure as in Synthesis Example 17 to obtain the target compound C-160 (6.24 g, 87% yield).

MS [M + 1] ⁺ 793

Synthesis Example 27 Synthesis of C-164

Except for using BCZ-5 (5.02 g, 10.00 mmol) instead of BCZ-1 was the same procedure as in Synthesis Example 14 to obtain the target compound C-164 (6.01 g, 82% yield).

MS [M + 1] ⁺ 733

Synthesis Example 28 Synthesis of C-168

Except for using BCZ-5 (5.02 g, 10.00 mmol) instead of BCZ-1 was the same procedure as in Synthesis Example 17 to obtain the target compound C-168 (6.47 g, yield 80%).

MS [M + 1] ⁺ 809

Examples 1 to 25 Fabrication of Green Organic EL Devices

Compounds synthesized in Synthesis Examples 1-9 and 13-28, respectively, were subjected to high purity sublimation purification by a conventionally known method, and then green organic EL devices were manufactured according to the following procedure.

First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then the substrate is cleaned for 5 minutes by UV and vacuum evaporator The substrate was transferred to.

M-MTDATA (60 nm) / TCTA (80 nm) / Compounds Synthesized in Synthesis Examples 1-9, 13-28 + 10% Ir (ppy) ₃ (30nm) / BCP (10 nm) on the thus prepared ITO transparent electrode An organic EL device was fabricated by laminating in order of / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm).

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , CBP and BCP are as follows.

[Comparative Examples 1 and 2] Fabrication of Green Organic EL Device

A green organic EL device was manufactured in the same manner as in Example 1, except that CBP and Ref-1 were used as emission host materials in forming the emission layer.

The structure of Ref-1 used is as follows.

[Evaluation Example 1]

For each of the green organic EL devices produced in Examples 1 to 25 and Comparative Examples 1 to 2, the driving voltage, current efficiency, and emission peak at current density (10) mA / cm 2 were measured, and the results are shown in Table 2 below. Shown in

TABLE 2

Sample	Host	Drive voltage (V)	EL peak (nm)	Current efficiency (cd / A)
Example 1	C-10	6.64	517	40.8
Example 2	C-12	6.57	517	40.9
Example 3	C-16	6.46	518	41.9
Example 4	C-28	6.51	518	41.1
Example 5	C-66	6.51	518	41.1
Example 6	C-68	6.59	517	41.7
Example 7	C-94	6.65	518	40.1
Example 8	C-96	6.49	518	41.9
Example 9	C-99	6.59	518	41.5
Example 10	C-117	6.50	519	40.6
Example 11	C-120	6.60	517	41.8
Example 12	C-122	6.55	517	40.9
Example 13	C-123	6.44	516	41.3
Example 14	C-124	6.50	518	41.5
Example 15	C-129	6.45	518	41.5
Example 16	C-132	6.50	519	41.9
Example 17	C-134	6.60	518	40.8
Example 18	C-135	6.45	517	40.5
Example 19	C-136	6.55	518	41.5
Example 20	C-144	6.60	517	41.8
Example 21	C-148	6.60	519	41.5
Example 22	C-156	6.55	517	40.9
Example 23	C-160	6.40	516	41.9
Example 24	C-164	6.50	518	41.8
Example 25	C-168	6.52	518	42.0
Comparative Example 1	CBP	6.93	516	38.2
Comparative Example 2	Ref-1	6.75	517	40.2

As shown in Table 2, the organic EL device of Example 1-25 using the compound according to the present invention as a light emitting layer of the green organic EL device, the green organic EL of Comparative Examples 1 to 2 using conventional CBP and Ref-1 Compared with the device, it was found to show better performance in terms of efficiency and driving voltage.

Examples 26 to 28 Fabrication of Red Organic EL Devices

Compounds (C-25, C-26, C-27) synthesized in Synthesis Examples 10 to 12 were subjected to high purity sublimation purification by a conventionally known method, and then a red organic electroluminescent device was manufactured according to the following procedure.

First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then washed the substrate for 5 minutes using UV and vacuum The substrate was transferred to the evaporator.

M-MTDATA (60 nm) / TCTA (80 nm) / C-25, C-26, C-27 compound + 10% (piq) ₂ Ir (acac) (30nm) / BCP ( 10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) was laminated to fabricate an organic EL device.

Comparative Example 3 Fabrication of Red Organic EL Device

A red organic EL device was manufactured in the same manner as in Example 26, except that CBP was used as the emission host material in forming the emission layer.

The structures of m-MTDATA, (piq) ₂ Ir (acac), CBP and BCP used in Examples 26 to 28 and Comparative Example 3 are as follows.

[Evaluation Example 2]

For each organic electroluminescent device fabricated in Examples 26-28 and Comparative Example 3, the driving voltage and current efficiency at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 3 below.

TABLE 3

Sample	Host	Drive voltage (V)	Current efficiency (cd / A)
Example 26	C-81	4.91	13.1
Example 27	C-82	4.95	12.4
Example 28	C-83	4.84	12.6
Comparative Example 3	CBP	5.25	8.2

As shown in Table 3, the organic electroluminescent device of Examples 26 to 28 using the compound according to the present invention as a material of the light emitting layer of the red organic electroluminescent device is a red color of Comparative Example 3 using the conventional CBP as a material of the light emitting layer Compared with the organic electroluminescent device, it was found to exhibit excellent performance in terms of efficiency and driving voltage.

Claims (9)

1. Compound represented by the following formula (1):

   [Formula 1]

   

   In Chemical Formula 1,

   Ar ₁ is a substituent represented by the following formula (2);

   [Formula 2]

   

   In Chemical Formula 2,

   L is a single bond, a substituted or unsubstituted C ₆ -C ₄₀ arylene group, or a substituted or unsubstituted heteroarylene group having 5 to 40 nuclear atoms;

   X ₁ to X ₅ are the same as or different from each other, each independently N or C (R ₁₁ ), and include at least one N,

   In this case, when two or more of X ₁ to X ₅ is C (R ₁₁ ), a plurality of R ₁₁ are the same or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryl Oxy group, substituted or unsubstituted C ₁ -C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ -C ₄₀ arylamine group, substituted or unsubstituted C ₁ -C ₄₀ alkylsilyl group, substituted or Unsubstituted C ₁ to C ₄₀ alkylboron group, substituted or unsubstituted C ₆ to C ₄₀ arylboron group, substituted or unsubstituted C ₆ to C ₄₀ arylphosphine group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted C ₆ ~ C ₄₀ aryl selected from the group consisting of silyl groups, or groups or grain to which they are adjacent To which they are attached may form a condensed ring;

   R ₁ to R ₃ are the same as or different from each other, and each independently deuterium (D), halogen, cyano, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkene Nyl group, substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ Alkyloxy group, substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl groups, substituted or unsubstituted heterocycloalkyl groups having 3 to 40 nuclear atoms, substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl groups, substituted or unsubstituted C ₁ to C ₄₀ alkylboron groups , a substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ Reel phosphine oxide group, and a substituted or non-substituted aryl group is selected from the group consisting of silyl unsubstituted C ₆ ~ C _40;

   Wherein R _1, R ₂ and R ₃ when present is a plurality of, respectively, a plurality of R _1, R ₂ and R ₃ are the same or different from each other,

   a, b and c are each independently an integer of 0-5,

   In the above L, R ₁ to R ₃ and R ₁₁ , C ₆ ~ C ₄₀ arylene group, a heteroarylene group of 5 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, C ₆ ~ aryl silyl group of C _40, each independently selected from deuterium, halogen, a cyano group , C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₄₀ Aryl group, nuclear atom 5 to 40 heteroaryl group, C ₆ ~ aryloxy group of C _40, C ₁ ~ C ₄₀ of the alkyloxy group, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl of Al Group, nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ aryl of C ₄₀ It may be substituted with one or more substituents selected from the group consisting of a phosphine group, a C ₆ ~ C ₄₀ aryl phosphine oxide group and a C ₆ ~ C ₄₀ arylsilyl group.
2. The compound of claim 1, wherein the compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 3 to 7.

    [Formula 3]

   

   [Formula 4]

   

   [Formula 5]

   

   [Formula 6]

   

   [Formula 7]

   

   In Chemical Formulas 3 to 7,

   Ar ₁ is the same as defined in Formula 2, and each Ar ₁ is the same or different,

   Z ₁ is selected from O, S, Se, N (R ₄ ), C (R ₅ ) (R ₆ ) and Si (R ₇ ) (R ₈ )

   R ₄ to R ₈ are the same as or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group , Substituted or unsubstituted C ₆ -C ₄₀ arylamine group, substituted or unsubstituted C ₁ -C ₄₀ alkylsilyl group, substituted or unsubstituted C ₁ -C ₄₀ alkylboron group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group and substituted or unsubstituted C ₆ Or an arylsilyl group of ˜C ₄₀ , or combine with an adjacent group to form a condensed ring Is a compound.
3. The compound of claim 1, wherein the substituent represented by Chemical Formula 2 is selected from a substituent group consisting of Chemical Formulas A-1 to A-15.

   

   In Chemical Formulas A-1 to A-15,

   L and R ₁₁ are the same as defined in Formula 1,

   When there are a plurality of R ₁₁ , they are the same as or different from each other,

   R ₂₁ is hydrogen, deuterium (D), halogen, cyano group, substituted or unsubstituted C ₁ -C ₄₀ alkyl group, substituted or unsubstituted C ₆ -C ₄₀ aryl group, substituted or unsubstituted nuclear atom 5 to 40 heteroaryl groups, substituted or unsubstituted C ₆ to C ₄₀ aryloxy groups, substituted or unsubstituted C ₁ to C ₄₀ alkyloxy groups, substituted or unsubstituted C ₆ to C ₄₀ aryl An amine group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ to C ₄₀ aryl boron group, substituted or aryl phosphonium the unsubstituted C ₆ ~ C ₄₀ pingi, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted selected from the group consisting arylsilyl of a C ₆ ~ C ₄₀ ring, or Or they may combine with adjacent groups to form a condensed ring,

   n is an integer of 0-4.
4. The compound of claim 3, wherein the formulas A-1 to A-15 are selected from the group of substituents consisting of the following substituents.

   
5. The compound of claim 1, wherein L is a single bond, a phenylene group, or a biphenylene group.
6. The method according to claim 1, wherein R ₁ to R ₃ are the same as or different from each other, each independently represent a C ₆ ~ C ₄₀ aryl group,

   Wherein a plurality of R ₁ to R ₃ are the same or different from each other.
7. The compound of claim 1, wherein the compound represented by Chemical Formula 1 is selected from the group consisting of compounds represented by Chemical Formulas C-1 to C-168.

   

   

   

   

   

   
8. An anode, a cathode, and one or more organic material layers interposed between the anode and the cathode;

   At least one of the one or more organic material layers comprises the compound according to any one of claims 1 to 7.
9. The organic electroluminescent device according to claim 8, wherein at least one of the one or more organic material layers containing the compound is a phosphorescent light emitting layer.